Hydrochloric Acid → HCID 58409154, compound

HRID 467973Notes

Reaction equation

HRID 467973 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C@@H:10]2[CH2:14][CH2:13][CH2:12][N:11]2[C:15]([C:17]2[C:18]([CH:23]([F:25])[F:24])=[N:19][N:20]([CH3:22])[CH:21]=2)=[O:16])=[O:9])=[CH:4][CH:3]=1.[BH4-].[Na+].Cl>CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:9])[C@@H:10]2[CH2:14][CH2:13][CH2:12][N:11]2[C:15]([C:17]2[C:18]([CH:23]([F:25])[F:24])=[N:19][N:20]([CH3:22])[CH:21]=2)=[O:16])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 44595546HCID 44595546, compound

Product 1

HCID 58409154HCID 58409154, compoundYield 83.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (4-chloro-phenyl)-[(S)-1-(3-difluoromethyl-1-methyl-1H-pyrazole-4-carbonyl)-pyrrolidin-2-yl]-methanone (370 mg; 1.0 mmol), which was prepared as described in example P5, in methanol (5 ml) at 0° C. was added portionwise sodium borohydride (35 mg; 1.0 mmol). The reaction mixture was stirred for 0.5 hours and 1N HCl was added until pH 7 reached. Solvent was removed under pressure and the remaining mixture was extracted with ethylacetate (2×20 ml). The combined organic layer was dried over Na2SO4, filtered, concentrated and dried in vacuo to give 0.31 g (83.3% of theory) of {(S)-2-[(4-chlorophenyl)-hydroxy-methyl]-pyrrolidin-1-yl}-(3-difluoromethyl-1-methyl-1H-pyrazol-4-yl)-methanone as an oil.

Workup

  1. customSolvent was removed under pressure
  2. extractionthe remaining mixture was extracted with ethylacetate (2×20 ml)
  3. dry with materialThe combined organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customdried in vacuo

Sources & evidence

ORD record
ord-dc4c722997654af48d7438ffba0ec94e
Source dataset
uspto-grants-2014_01
Patent number
US08623902B2

Reaction notes

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